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Paper | Regular issue | Vol 65, No. 2, 2005, pp.319-327
Published online, 17th December, 2004
DOI: 10.3987/COM-04-10262
The First Synthesis of (S)-(+)-Cacalol

Shin Tanikawa, Michiko Ono, and Hiroyuki Akita*

*School of Pharmaceutical Sciences, Toho University, 2-2-1, Miyama, Funabashi, Chiba 274-8510, Japan

Abstract

The first synthesis of (S)-(+)-cacalol (1) was achieved by a combination of the BF3·Et2O–mediated reaction of (S)-4,5-epoxy-(2E)-pentenoate (7) with 3,4-dimethoxytoluene to give (S)-4-aryl-5-hydroxy-(2E)-pentenoate (5) and consecutive conversion of (S)-5 into (S)-1.